Heating 3,3-dimethylbut-1-ene with strictly anhydrous gas yields a major substitution product. Which — Haloalkanes and Haloarenes Chemistry Question
Question
Heating 3,3-dimethylbut-1-ene with strictly anhydrous $HCl$ gas yields a major substitution product. Which distinct rearrangement dictates this final chemical structure?
Answer: B
💡 Solution & Explanation
Initial protonation forms a $2^\circ$ carbocation adjacent to a quaternary carbon. A rapid 1,2-methyl shift generates a significantly more stable $3^\circ$ carbocation, which is subsequently attacked by $Cl^-$ yielding 2-chloro-2,3-dimethylbutane.
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